Benzaldehyde → rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-phenyl-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 428705

Reaktionsgleichung

Reaktionsgleichung von HRID 428705
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[CH:4].C([Mg]Cl)#C.C(=O)C1C=CC=CC=1.Br[C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1/[C:26](=[CH:34]/[C:35]1[NH:36][CH:37]=[CH:38][C:39]=1[O:40][CH3:41])/[C:27](=[O:33])[NH:28]2>[Cu]I.CN(C=O)C.CCN(CC)CC>[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[C:4][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1/[C:26](=[CH:34]/[C:35]1[NH:36][CH:37]=[CH:38][C:39]=1[O:40][CH3:41])/[C:27](=[O:33])[NH:28]2

Komponenten

8

Edukt 4

HCID 240BenzaldehydeHCID 20155alpha-EthynylbenzenemethanolHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×HCID 178462451HCID 178462451, Verbindung

Produkt 1

HCID 9969383rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-phenyl-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Using Method D above, 3-hydroxy-3-phenyl-1-propyne (0.1 g, 0.78 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to benzaldehyde (Aldrich) through Method A above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (0.1 g, 0.31 mmol) (Starting Material 1) using DPPFPdCl2 (12.6 mg) (Aldrich) and CuI (3 mg) (Aldrich) as catalyst in DMF (5 mL) and Et3N (5 mL) as solvent at 85° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-phenyl-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 42 mg, 38%).

Quellen und Nachweise

ORD-Eintrag
ord-023af678f9a34135891f01370728af4e
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313310B1

Verknüpfte Notizen

Wird geladen…